Ethanol → 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acid

HRID 51596Notes

Reaction equation

HRID 51596 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][C:27](=[CH:30][C:31]([OH:33])=[O:32])[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+].C(O)C.O>[Pd].C(O)(=O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([CH:24]3[CH2:25][CH2:26][CH:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][CH2:29]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 227362722-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyliden}acetic acid

Product 1

HCID 227363252-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acidYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyliden}acetic acid (0.60 g, 1.36 mmol), 10% palladium on activated carbon (0.18 g), 1M aqueous sodium hydroxide (9 mL) and ethanol (60 mL) was hydrogenated under an atmosphere of hydrogen (60 psi) for 20 hours and filtered through a pad of celite. The filtrate was evaporated under reduced pressure to yield a white solid which was taken into water (20 mL) followed by addition of 1M acetic acid (20 mL) to precipitate the product. The suspension was then filtered and the solid was lyophilized to yield 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acid (0.51 g, 1.15 mmol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 11.99(br, 1H), 8.13(s, 1H), 7.60 (s, 1H), 7.49(d, 2H), 7.41(t, 2H), 7.15(t, 1H), 7.09(m, 4H), 6.09(br, 2H), 4.60 (m, 1H), 2.20-1.24(m, 11H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% acetonitrile-0.05M ammonium acetate over 10 min, 1 mL/min) Rt 9.62 min. MS: MH+ 443.

Workup

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate was evaporated under reduced pressure
  3. customto yield a white solid which
  4. customto precipitate the product
  5. filtrationThe suspension was then filtered

Sources & evidence

ORD record
ord-33e96da39b5d4515844028d848d1e653
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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